With more than 700 islands to choose from, the Caribbean caters for all
tastes. Our destination expert Fred Mawer picks the best and outlines what
each has to offer

When to go

There are three factors to consider when choosing your Caribbean holiday: weather, cost and crowds. The weather in the Caribbean is generally best – namely driest, with low humidity and pleasantly cool nights – December through to April. Summer and autumn are stickier, a few degrees warmer and wetter: showers and short, heavy downpours are common, prolonged spells of constant rain less so. June to November is also the official hurricane season. Statistically, September, followed by October, are the months you’re most likely to encounter a major storm, though even then the odds are slim. It partly depends on which island you go to, as some are more hurricane-prone than others - see stormcarib.com.

In terms of cost, mid-December to mid/late April is peak season in the Caribbean, and hotel (and villa) rates are 20-50 per cent higher then than the rest of the year. For travel during any school holiday period, you’ll pay a premium for flights.

As for crowds, hotels are fullest and the beaches most crowded in the peak winter months, especially Christmas/New Year, February and Easter. September and October are the quietest months, when some hotels and restaurants close, and bars can be near empty.

Taking into account the weather, cost and crowds, May is an ideal month to visit. The weather then is often almost as good as in the peak winter months, but accommodation costs significantly less. For similar reasons, the first half of December is also a good time to travel. If you’re tied to the school holidays and intent on keeping costs down, consider travelling over May half term, when flights can work out cheaper than other school holiday periods. If you want to go in the school summer holidays, note that fares tend to drop in late August.

The islands

Click on the links below to read about individual islands. We have detailed expert guides on Antigua, Barbados, Grenada, Jamaica, Nevis, St Kitts and St Lucia, and for the other islands and island groups, we have summarised their appeal, indicated what they are best for, and given pointers on when to consider visiting. Bear in mind that the advice on when to go, above, applies across the Caribbean.

Booking advice

Flights

The two main airlines flying from the UK to the Caribbean islands are British Airways (ba.com) and Virgin (virgin-atlantic.com). In the irregular but frequent sales offered by BA and Virgin, economy tickets start at around £460-£600 return, depending on the island. For travel at peak times such as school holiday periods, you may well have to pay several hundred pounds more. It’s well worth contacting a good flight specialist such as Trailfinders (trailfinders.com) or DialAflight (dialaflight.com) to help find best fares and most convenient routes. Some "direct" services in fact involve a brief stop en route at another island – for example, British Airways’ flights to St Kitts go via Antigua. Though you don’t need to leave the plane, this arrangement can add at least an hour to the overall journey time, so before booking check if the service is non-stop or not.

Charter airlines – Monarch (monarch.co.uk), Thomas Cook (thomascookairlines.com) and Thomson (thomson.co.uk/flights) – also fly to some islands, sometimes from regional UK airports. Their seat-only fares can be lower than with the scheduled carriers, particularly for last-minute bookings.

To reach some lesser islands, and for multi-centre trips, you need to take an inter-island flight. Liat (liat.com) is the main, but not always reliable, carrier. There are a number of other small, regional airlines – tour operators can advise about options. Inter-island flights are not cheap, so to keep costs down choose an island to which you can fly direct.

For advice on how to reach specific islands, click through on the links above to the islands' individual guides.

Tour operators

Booking a package to the Caribbean is likely to work out cheaper than arranging the same trip independently, and you’ll have back up should things wrong (think hurricanes). Most Caribbean hotels can be booked with at least several, and sometimes many, tour operators, so shop around: package prices can vary a lot, and deals at hotels such as seven nights for the price of five are rarely unique to a particular operator.

Villas can be rented on many islands, and smarter ones come with a housekeeper and sometimes other staff. Caribbean villa specialists include CV Villas (020 7563 7999; cvvillas.com), Prestbury Worldwide Resorts (01625 858158; prestburyworldwideresorts.co.uk) and Wimco (0870 850 1144; wimco.com). For direct bookings (often cheaper), turn to homeaway.co.uk, which features thousands of villas and apartments across the region, many with useful reviews from previous guests. A good option for families is renting a villa or apartment in a hotel, giving you spacious accommodation combined with facilities such as restaurants and watersports; tour operators offer the best of these properties.

Cruise

For several reasons, the Caribbean is the world’s premier holiday spot for cruising. The weather is generally hot and sunny. You can visit half-a-dozen islands in a week – extensive, DIY island hopping in the Caribbean is not that easy or cheap, making a cruise definitely the best way to see a lot of the region in one go. On-shore activities are enormously varied, ranging from sightseeing in colonial cities to zip-lining over rainforests, climbing up waterfalls, snorkelling with stingrays and trying out all sorts of other watersports. Or you can just chill on a beach – several cruise lines include in their itineraries a stop at their own, private tropical island. The choice of non-cultural excursions makes Caribbean cruising an ideal option for families.

As for possible downsides, many Caribbean cruising itineraries visit a port most days, so there’s often little daytime at sea relaxing. Cruise-ship passengers can swamp the ports they visit. And while independent exploring is easy on stops on Mediterranean cruises, in the Caribbean transport is usually required to reach key sights, so many passengers sign up for expensive, organised excursions.

There are three cruising areas in the region: the Eastern Caribbean, typically including Puerto Rico, the Virgin Islands and, for Florida departures, the Bahamas; the western Caribbean, taking in the Cayman Islands, Jamaica and Mexico; and the Southern Caribbean, visiting southerly Windward Islands and the Dutch Antilles.

Cruise-and-stay packages are worth considering. Many cruises set off from Florida, but Barbados is also an important embarkation point. There are also good-value repositioning cruises in the spring and autumn, crossing the Atlantic by sea one way, flying the other.

You can cruise in the Caribbean year round. The weather is best December-April, the peak season, though ports are busiest then, and prices are lower at other times of year. If you go in the hurricane season (especially September and October), there is a chance that your ship will have to change its itinerary to avoid storms. Visit telegraph.co.uk/travel/cruises for more details.